Around 1760, Hugh Craig of County Down, Ireland, moved his family to Virginia, where they were instrumental in the organization of Chesterfield Co., Virginia. Hugh had three sons, John, James, and Alexander. During the American Revolution, John served as a patriot in South Carolina. Liking what he had seen, he and his brother Alexander relocated from Virginia to the area that is now Chesterfield. Between January 21, 1785 and May 16, 1799, Alexander received 7 land grants in Cheraw District totaling 2655 acres.

John on February 22, 1797, married Sarah Chapman, daughter of James Chapman of Virginia and built her a house, still known as the Craig house, it is the oldest house in Chesterfield. Soon Sarah's brother, John, with his wife moved into the area, and these comprised the first two families in the town.

The South Carolina County Court Act of 1785, divided what had been Cheraw District, into three separate counties, Darlington, Marlboro, and Chesterfield. The Craig homeplace was chosen to be where the new county built its courthouse. The county, by tradition, was named after Chesterfield Co., Virginia, through the influence of the Craig family. However most materials state, the county was named after Lord Chesterfield, Philip Dormer Stanhope, a close friend of George III, for which Chesterfield Co., Virginia was named.

In 1819, Report 1, of the Civil and Military Engineer, the following was recommended: "The roof of the Court House of this district will require to be new shingled and painted. The outside Walls and the Window Shutters and the Doors to be painted. The Roof of the Gaol to be repaired and painted; all the outside Shutters, outer Doors, Window Sashes and Frames to receive one coat of paint. I would respectfully recommend that an appropriation of six hundred dollars be made for these objects." As a result in the Report of the Commissioner For the Department of Public Buildings, to the Board of Public Works, for the year 1820, it is stated "A proposal has been made for executing the repairs required to the court house and gaol in this district and the workman has been ordered to proceed with the work. The court house is a wooden building, two stories high, and measures 34 by 24 feet, This building has been standing some time, but it is in tolerable repair, has been well kept, and is considered sufficiently large for the business of the district. The gaol is a substantial brick building , two stories high, and measures 40 by 36 feet---there are four rooms on the first floor, and five on the second, which are well arranged." John Chapman was paid September 4, 1820 for the repairs completed by him on the Court House and Gaol. It appears as though the Craig family, who where very involved in county politics, took pride in their little town and the buildings within.

Chesterfield became largely an industrial town. By 1845, located in town were an iron foundry, fur hat factory, blacksmith shop, cabinet and furniture shop, harness and shoe shop, wheelwright shop, a flour, grist and saw mill. At this time the population was 50 whites and 250 blacks.

On November 19, 1860, Chesterfield County held the first Secession meeting held in South Carolina. Local leaders at that meeting were Col. Stephen Jackson, Senator James White Whitney, Col. McFarland, Col. Prince, Col. H. McIver, Chancellor Inglish, General E.B.C. Cash, and Col. Alfred Lowery, an ex-senator. The ensuing War took a terrible toll on the inhabitants of the County.

The town was the site where many of the men and boys of Chesterfield Co., signed up in Confederate States Army "for the duration of the war". Many would not return.

On March 2, 1865, the 123^rd New York Inf, 20^th Division, entered Chesterfield skirmishing with Butler's Confederate Cavalry. A stand was made on the east side of Thompson's Creek, after the bridge had been burned, which held the Union Troops in Chesterfield till the next day. Sherman spent the night there also sleeping in the Craig house. Chesterfield was recorded as a '"dirty little town" at about twenty houses, one hotel, and a court house.' ( Sherman's March Through The Carolinas, John G. Barrett, page 106) About a mile on the east side of the Thompson Creek bridge is a lone grave which marker reads "A Confederate Soldier Unknown Georgia Boy, Erected by Stonewall UDC", apparently a casualty of the skirmish the day before. Before leaving the town, the Court House was burned with all the records except one Deed Book that partially survived.

In 1872, Chesterfield was incorporated. Until 1900, Chesterfield was connected to Cheraw and the other communities by post road, but then the Cheraw-Lancaster Railroad arrived, bringing greater trade with other areas of the State. The railroad was removed in 1941, being replaced by trucking.

Chesterfield has continued to grow, and has prospered. Highway #9, bypasses just to the south of Main Street, a wide street lined on both sides with the town businesses and shops. The current mayor, John Douglas says "There are a lot of things that make Chesterfield special that you don't find in other towns our size, (1990 population 1,373), an active downtown, four park areas, and a very active urban forestry program, and a community center. Chesterfield shows how a town can have growth but maintain its small town atmosphere." Still the main industry in Chesterfield is government, for the town and for the County.